As a Star Trek fan, I put First Contact at the top, followed by Wrath of Khan. I qualify that, because I agree with the earlier comment that Khan might stand on its own better to a non-fan.
First Contact wins for several reasons, one of which is the funny moments were few, but really worked well.
I always loved Data jumping down and being riddled with machine gun bullets. Then he turns around and takes a few more rounds, looks up and smiles warmly. “Greetings!”
And the Lt. Barkely cameo was unexpected and funny.
Data also announces in that movie that he’s disconnecting his emotion chip before going into a scary battle against the Borg, and Picard says, “There are times when I envy you, Mr. Data.”
“Wrath of Khan” had plenty of funny moments as well, although its humor was more understated (and consequently funnier, IMO):
-The Kirk/Bones banter after the Kobayashi Maru (“What about my performance?”)
-"‘It was the best of times, it was the worst of times.’ Message, Spock?" “None that I am aware of - except, of course, happy birthday.”
-McCoy’s riffing on the “Beware of Greek bearing gifts” line
-Kirk muttering “I hate inspections” (and then later cutting the actual inspection short after about two minutes so he can go check out the bridge)
-Spock’s wry “That is wise” after Kirk declines to argue against his logic
-McCoy sputtering “You green-blooded, inhuman…”
The Undiscovered Country is my favorite. Perhaps because it includes the most important decision Kirk ever made: “We surrender!!” That scene gives me goosebumps.
I bought Nemesis today. It was the first time I had seen it in years. I enjoyed it. I would rank the movies, but I’ve never seen 1, 3, and 5 and I haven’t seen Insurrection since it came out. I’ve seen all the rest in the last month though.
(Why, yes, I am a geek!)